Holiday rentals in Sharptown

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1‑bedroom studio on a quiet street in historic Delmar, MD. Kylan Barn – 6 min. Venue 54 – 7 min. Downtown Salisbury – 15 min. SU – 20 min. OCMD – 45 min. Sleeps 4 with king bed and full pull‑out couch. Workspace, fast WiFi, kitchenette, private laundry. Safe neighborhood, off‑street parking, well‑lit walkways. Private backyard patio with 6' fence. Stylish, super clean and comfortable. Sorry....no 3rd‑party bookings, pets, parties, indoor smoking or cooking.

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

1900's Modern Farmhouse on 7.5 private acres

Welcome to our 1900's farmhouse. This home has been lovingly updated and maintained over the past century, and sits on 7.5 acres. While it is private and peaceful, its location is minutes away from everything making it easy to get around. Enjoy spacious living and endless outdoor fun in our dedicated game barn (ping pong, cornhole!) and large pastures (frisbee golf, soccer!). This family-friendly home blends historic charm with modern comforts, perfect for creating unforgettable memories.

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Retro Hipster: Close to downtown, dining and fun

Want to stay in a place with a Jazzy retro style?  This is the perfect place for you.  This renovated 2 bedroom, 2 bath apartment features beautiful riverfront views, high ceilings, wifi, smart TV’s and a bit of History.  This is part of a hotel from the Green Book era where Etta James and Billie Holiday both stayed. This space is perfect for business travelers, couples and families looking for place near in downtown Salisbury or a short drive from the beach.

Secluded Waterfront 15mi to Beach•Kayaks•Fast WiFi

Casa Blue Heron is a 2,254 ft² (209 m²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature... Wish I had booked an extra day!" Add us to your wish list by clicking the❤️in the upper-right corner.

Stella

Welcome to Stella! She has been lovingly restored by our family and carefully designed by our son who owns JoonMoon Design with his beautiful wife. We are a family who loves to travel and discover places of rest. Stella was designed with that in mind. She is approachable, comfortable and invites you to kick off your shoes and relax. She is walking distance to Salisbury University and close to many restaurants and stores.

Cozy home in Seaford

Relax with your family in this quiet & peaceful home located in the heart of Seaford Located near state parks to hike, hunt, fish A short 50-minute drive to the Delaware beaches Conveniently located 5 minutes from Heritage Shores golf course and wedding venue Less than 5 miles from Vanderwende Acres and Willowbrook Weddings 5-10 minutes from Walmart, Dunkin Donuts, Starbucks, and many fast food option